Fumaric Acid is added to foods as an acidity regulator and flavoring agent and may be used as a substitute for cream of tartar. Typical products include bread, fruit drinks, pie fillings, poultry, wine, jams, and jelly.
Fumaric Acid is used as a mordant in dyeing and in the manufacture of synthetic resins and polyhydric alcohols.
Fumaric acid (E297) is a four-carbon dicarboxylic acid used as a food acidity regulator.
Fumaric acid is often a beverage ingredient but applies to bakery products, powdery dessert mixes, and confectionary.
Next to food applications, fumaric acid is used in feed as an antibacterial agent.
Fumaric acid is a well-known chemical used in the production of polymers and as an intermediate in the production of L-malic and L-aspartic acids.
Fumaric acid is predominantly produced by petroleum-based chemical synthesis.
However, research focusing on microbial fumaric acid production from starchy materials is optimizing and commercializing this ‘green’ technique.
The salts and esters are known as fumarates. Fumarate can also refer to the C4H2O2−4 ion (in solution).
Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.
Uses
Food
Fumaric acid has been used as a food acidulant since 1946.
Fumaric acid is approved as a food additive in the EU, USA, Australia, and New Zealand.
As a food additive, it is used as an acidity regulator and can be denoted by the E number E297.
Fumaric acid is generally used in beverages and baking powders for which requirements are placed on purity.
Fumaric acid is used in making wheat tortillas as a food preservative and leavening acid.
Fumaric acid is generally used as a substitute for tartaric acid and occasionally in place of citric acid, at a rate of 1 g of fumaric acid to every ~1.5 g of citric acid, to add sourness, similarly to the way malic acid is used.
As well as being a component of some artificial vinegar flavors, such as "Salt and Vinegar" flavored potato chips, it is also used as a coagulant in stove-top pudding mixes.
The European Commission Scientific Committee on Animal Nutrition, part of DG Health, found 2014 that fumaric acid is "practically non-toxic," but high doses are probably nephrotoxic after long-term use.
Medicine
Fumaric acid was developed as a medicine to treat psoriasis autoimmune condition in the 1950s in Germany as a tablet containing three esters, primarily dimethyl fumarate, and marketed as Fumaderm by Biogen Idec in Europe.
Biogen would later develop the primary ester, dimethyl fumarate, as a treatment for multiple sclerosis.
In patients with relapsing-remitting multiple sclerosis, the ester dimethyl fumarate (BG-12, Biogen) significantly reduced relapse and disability progression in a phase 3 trial.
It activates the Nrf2 antioxidant response pathway, the primary cellular defense against the cytotoxic effects of oxidative stress.
Other uses
INDUSTRIES
Fumaric acid has various applications in different industries.
Here are some common uses of fumaric acid:
Food and Beverage Industry: Fumaric acid is used as a food additive, primarily as an acidulant and flavor enhancer.
Fumaric acid is often found in beverages, fruit-flavored drinks, candies, gelatin desserts, baking powders, and other food products.
Fumaric acid provides a sour taste similar to citric acid and helps preserve and enhance the flavor of food and beverages.
Cosmetics and Personal Care Products: Fumaric acid has applications in cosmetic formulations and personal care products.
Fumaric acid is applied as an ingredient in creams, lotions, and ointments, where it functions as a pH adjuster, buffering agent, and skin-conditioning agent.
Resins and Polymers: Fumaric acid produces unsaturated polyester resins (UPR) and alkyd resins.
Fumaric acid acts as a crosslinking agent and helps enhance the properties of these resins, including their strength, durability, and heat resistance.
Cleaning Products: Fumaric acid is utilized in certain cleaning products, such as detergents and dishwashing liquids.
Fumaric acid aids in removing dirt, stains, and scale deposits due to its acidic properties.
Fumaric acid is used to manufacture polyester resins, polyhydric alcohols, and as a mordant for dyes.
When fumaric acid is added to their feed, lambs produce up to 70% less methane during digestion.
Identifiers
CAS Number: 110-17-8
EC / List no.: 203-743-0
CAS no.: 110-17-8
Mol. formula: C4H4O4
Chemical formula: C4H4O4
Molar mass: 116.072 g·mol−1
Appearance: White solid
Density: 1.635 g/cm3
Melting point: 287 °C (549 °F; 560 K) (decomposes)[2]
Solubility in water: 4.9 g/L at 20 °C[1]
Acidity (pKa)
pka1 = 3.03, pka2 = 4.44 (15 °C, cis isomer)
Magnetic susceptibility (χ): −49.11·10−6 cm3/mol
Dipole moment: non zero
Fumaric Acid
It is often used as a beverage ingredient but also finds application in bakery products, powdery dessert mixes, and confectionary (Santini et al., 2012).
Next to food applications, fumaric acid is used in feed as an antibacterial agent and is a well-known chemical used in the production of polymers and as an intermediate in the production of L-malic and L-aspartic acid.
Fumaric acid is predominantly produced by petroleum-based chemical synthesis, but research focusing on microbial fumaric acid production (e.g., using Rhizopus oryzae) from starchy materials is in the process of optimizing and commercializing this ‘green' technique (Xu et al., 2012; Yang et al., 2011; Alonso et al., 2014).
Fumaric acid is used as a food ingredient in beverages and baking powders.
Furthermore, fumaric acid is a pharmaceutically active substance used to treat psoriasis or multiple sclerosis (Gold et al., 2011).
The current world market is about 90,000 t y-1. However, particular interest in fumaric acid - as in all dicarboxylic acids described in this chapter - is derived from its suitability as a building block chemical.
Use as a bulk chemical in the polymer industry is conceivable.
Also, its chemical relatedness to aspartic acid, a precursor for aspartame, a widely used sweetener, makes it an interesting product, provided that the production costs are low enough.
Originally, fumaric acid was isolated from plants belonging to the genus Fumaria, from which its name is derived.
Applications
Fumaric acid has been used in food and beverage products since 1946.
Fumaric Acid is currently used in wheat and corn tortillas, sourdough and rye bread, refrigerated biscuit doughs, fruit juice and nutraceutical drinks, gelatin desserts, gelling aids, pie fillings, and wine.
Food research shows that Fumaric acid improves quality and reduces the costs of many food and beverage products.
It is also used in animal feed.
Like malic acid, fumaric acid is a dicarboxylic acid with pK values of 3.03 and 4.44.
It has a strong acid taste, but a positive flavor effect is that it blends with certain flavors to intensify its aftertaste.
Fumaric acid is used in fruit drinks, gelatine desserts, pie fillings, biscuit doughs, and wines.
It is naturally present in rice, sugar cane, wine, plant leaves, mushrooms, and gelatine (Barbosa-Canovas et al., 1997).
Like citric acid, it also has antimicrobial properties, working as a chelator, binding micronutrients essential for bacterial growth.
As for malic acid, the antimicrobial mechanism for fumaric acid has only been investigated to a limited extent. One of the main effects is probably due to its pH lowering.
Fumaric acid, also known as fumarate or E297, belongs to the class of organic compounds known as dicarboxylic acids and derivatives.
These are organic compounds containing exactly two carboxylic acid groups.
Fumaric acid is a weakly acidic compound (based on its pKa). Fumaric acid exists in all living species, ranging from bacteria to humans.
Within yeast, fumaric acid participates in some enzymatic reactions.
It is formed by the oxidation of succinic acid by succinate dehydrogenase.
DETAILED APPLICATIONS
Animal Feed
Fumaric Acid has proven to be a particularly effective additive to piglet feed during the post-weaning period.
Including Fumaric Acid and the resultant adjustment of the pH value demonstrate improved weight gain, food consumption, and feed conversion ratio. Fumaric Acid remains longer in the gut and helps to maintain pH throughout, killing harmful microorganisms.
Industrial Uses
Industrial uses of fumaric acid include unsaturated polyester, alkyd resins, printing inks, paper sizing, and starch, and it helps lower reaction temperatures and modify properties.
Cleaning Agents for Dentures/Bath Salts
Fumaric Acid can be used with other ingredients to make cleaning agents for dentures and bath salts.
Low moisture absorption and solubility help to keep the integrity of formulations.
Tacos
The shelf life of dry tortilla mixes is extended because Fumaric Acid does not absorb moisture during storage and distribution.
In wheat flour tortillas, adding Fumaric Acid results in easily machined dough and faster production rates.
Bread
Fumaric Acid acts as an instant flavoring agent for rye and sourdough breads.
Fumaric Acid is added to dough ingredients during the dry blending step.
In English muffins, Fumaric Acid significantly increases porosity.
Dough machinability is improved, and more sourness is provided per unit weight.
Fruit Juice Drinks
Fumaric Acid provides more sourness per unit weight than other acidulants used in fruit juice drinks.
This substantially reduces the acidulant cost.
Using Fumaric Acid helps stabilize the pH of a fruit juice drink, stabilizing color and flavor.
Wine
Fumaric Acid can economically acidify wine with no detectable difference in flavor.
Fumaric Acid also prevents secondary fermentation after bottling and can act as a clarifier when low concentrations of copper and iron are present.
Confectioneries
Fumaric Acid extends the shelf life of acid-coated candies because it does not absorb moisture during storage and distribution. Maintaining a low moisture level retards sucrose inversion.
Gelatin Desserts
Fumaric Acid significantly reduces acidulant costs in gelatin desserts.
Fumaric Acid maintains non-caking and free-flowing qualities.
By keeping the moisture content low, fumaric acid helps maintain the stability of flavor components.
Fumaric Acid also increases gel strength so that food processors may reduce standard gelatin content by about 2%.
Pie Fillings
Fumaric Acid can be mixed directly with the starch and sugar ingredients in pie fillings.
Fumaric Acid lowers costs by reducing the quantity of food acid needed in product formulations.
Fumaric Acid also improves smoothness and extends the critical cook times for optimum gelation.
Egg White Foams
Fumaric Acid can promote maximum volume in egg-white foams and end products based on egg-white foams.
Confectioneries
Fumaric acid extends the shelf life of acid-coated candies because it does not absorb moisture during storage and distribution.
Maintaining a low moisture level retards sucrose inversion.
Acidulant cost is also reduced as fumaric acid provides more sourness per unit weight than other acidulants used in dry form.
Jellies and Jams
Fumaric acid can cut food acid costs when used as an acidulant for jams, jellies, and preserves.
As little as two pounds of fumaric acid can be used to replace every three pounds of Citric, Malic, or Tartaric acid. At the 2:3 replacement ratio, fumaric acid does not produce significant gel strength or pH differences.
